WO2011052762A1 - Procédé de production d'une dispersion de solvant organique composée de microparticules d'oxyde inorganique - Google Patents

Procédé de production d'une dispersion de solvant organique composée de microparticules d'oxyde inorganique Download PDF

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WO2011052762A1
WO2011052762A1 PCT/JP2010/069392 JP2010069392W WO2011052762A1 WO 2011052762 A1 WO2011052762 A1 WO 2011052762A1 JP 2010069392 W JP2010069392 W JP 2010069392W WO 2011052762 A1 WO2011052762 A1 WO 2011052762A1
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dispersion
zirconia
inorganic oxide
fine particles
titania
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PCT/JP2010/069392
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English (en)
Japanese (ja)
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敬一 長川
徳明 川▲さき▼
篤 宮田
宜寛 平田
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堺化学工業株式会社
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Priority to CA2778761A priority Critical patent/CA2778761A1/fr
Priority to RU2012122027/05A priority patent/RU2012122027A/ru
Priority to AU2010312371A priority patent/AU2010312371A1/en
Priority to EP10826892A priority patent/EP2495291A1/fr
Priority to US13/504,330 priority patent/US20120217456A1/en
Priority to CN2010800495184A priority patent/CN102575124A/zh
Priority to JP2011538514A priority patent/JP5776552B2/ja
Publication of WO2011052762A1 publication Critical patent/WO2011052762A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G9/00—Compounds of zinc
    • C01G9/02—Oxides; Hydroxides
    • C01G9/03—Processes of production using dry methods, e.g. vapour phase processes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G23/00—Compounds of titanium
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G23/00—Compounds of titanium
    • C01G23/04—Oxides; Hydroxides
    • C01G23/047—Titanium dioxide
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G25/00—Compounds of zirconium
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G25/00—Compounds of zirconium
    • C01G25/02—Oxides
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
    • C01G9/00—Compounds of zinc
    • C01G9/02—Oxides; Hydroxides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/36—Compounds of titanium
    • C09C1/3607—Titanium dioxide
    • C09C1/3684—Treatment with organo-silicon compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/12—Treatment with organosilicon compounds
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/80—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70
    • C01P2002/88—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70 by thermal analysis data, e.g. TGA, DTA, DSC
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/01—Particle morphology depicted by an image
    • C01P2004/03—Particle morphology depicted by an image obtained by SEM
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/01—Particle morphology depicted by an image
    • C01P2004/04—Particle morphology depicted by an image obtained by TEM, STEM, STM or AFM
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/10—Solid density
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/12—Surface area
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/22—Rheological behaviour as dispersion, e.g. viscosity, sedimentation stability
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values

Definitions

  • the present invention relates to a method for producing an organic solvent dispersion of inorganic oxide fine particles, and more particularly to a method for producing an organic solvent dispersion having excellent transparency of inorganic oxide fine particles selected from zirconia and titania.
  • fine particle dispersions of inorganic oxides such as silica, alumina, zinc oxide, tin oxide, zirconia, and titania have been used in various industrial fields, particularly in the optical field, to adjust the refractive index. It has been. Among these, zirconia and titania have a high refractive index and are used to increase the refractive index of optical materials. Conventionally, such a fine particle dispersion has been used in which the dispersion medium is water. However, in the field of optical films, since an aqueous dispersion is not easily kneaded with a resin component, it has recently been dispersed. There has been a strong demand for dispersions in which the medium is an organic solvent.
  • Patent Literature it has been proposed to add an organic solvent and a zirconia stabilizer such as acetic acid to an aqueous dispersion of zirconia fine particles, and replace the water with an organic solvent to obtain an organic solvent dispersion of zirconia fine particles.
  • Patent Literature a zirconia stabilizer such as acetic acid
  • the dispersion medium of zirconia fine particles is simply changed from water to an organic solvent, the zirconia fine particles are likely to aggregate and the transparency is not sufficient. Therefore, it has already been known that when an organic solvent dispersion of inorganic oxide fine particles is produced, it is effective to perform a surface treatment with a silane coupling agent in order to modify the inorganic oxide fine particles to be lipophilic. ing.
  • inorganic oxide fine particles are surface-treated with a silane coupling agent, an inorganic solvent having an amphiphilic organic solvent having a boiling point of 100 ° C. or higher, for example, 1-butanol as a dispersion medium, in order to enhance the effect of the surface treatment.
  • the dispersion of oxide fine particles is treated with a silane coupling agent under reflux to hydrolyze the silane coupling agent and to react with hydroxyl groups on the surface of the inorganic oxide fine particles. It has been proposed to chemically bond to the surface (see Patent Document 2).
  • the silane coupling agent when hydrolyzing the silane coupling agent at such a high temperature to surface-treat the inorganic oxide fine particles, the silane coupling agent itself is also dehydrated and condensed to become an oligomer, and sometimes has a high molecular weight. It is also known that it becomes insoluble in a solvent and precipitates. Thus, if the silane coupling agent has a high molecular weight and is insolubilized in a solvent, it adversely affects the transparency of the resulting dispersion.
  • organic solvent dispersions of zirconia and titania which have a high refractive index and excellent transparency, are widely used in the optical field, especially optical films including antireflection films, taking advantage of their properties.
  • the present invention has been made in order to solve the above-described problems in producing an organic solvent dispersion of inorganic oxide fine particles, and is an organic material having excellent transparency of inorganic oxide fine particles selected from zirconia and titania. It aims at providing the manufacturing method of a solvent dispersion.
  • an inorganic dispersion of fine inorganic oxide particles selected from zirconia and titania is mixed with a silane coupling agent at a temperature in the range of ⁇ 20 to 60 ° C. in the presence of an acid, and stirred.
  • a method for producing an organic solvent dispersion of inorganic oxide fine particles which comprises replacing the alcohol with a lipophilic organic solvent after surface-treating the oxide fine particles.
  • an organic solvent dispersion excellent in transparency of inorganic oxide fine particles selected from zirconia and titania can be obtained.
  • a fine particle organic solvent dispersion can be obtained.
  • it has been difficult to obtain a titania organic solvent dispersion excellent in transparency but according to the present invention, when the production conditions are optimally selected, the titania has higher transparency than the raw material dispersion.
  • An organic solvent dispersion can be obtained.
  • the method for producing an organic solvent dispersion of inorganic oxide fine particles comprises a silane cup at a temperature in the range of ⁇ 20 to 60 ° C. in the presence of an acid in an alcohol dispersion of inorganic oxide fine particles selected from zirconia and titania.
  • a second step of substituting the above-mentioned alcohol with a lipophilic organic solvent is a silane cup at a temperature in the range of ⁇ 20 to 60 ° C. in the presence of an acid in an alcohol dispersion of inorganic oxide fine particles selected from zirconia and titania.
  • the zirconia fine particle alcohol dispersion used in the first step is usually produced by a method in which zirconium oxychloride is hydrolyzed in water with heat or alkali, and then the dispersion medium is replaced with alcohol. Can also be used.
  • an alcohol dispersion of titania fine particles is usually produced by a method of hydrolyzing a titanium salt such as titanium tetrachloride and then substituting the dispersion medium with alcohol, but commercially available products can also be used.
  • the alcohol which is a dispersion medium in the alcohol dispersion of the fine particles of zirconia or titania is not particularly limited.
  • methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, t-butyl alcohol , Heptanol, cyclopentanol, cyclohexanol, octanol, lauryl alcohol and the like can be exemplified, but usually methanol, ethanol or isopropanol is preferably used, and methanol is particularly preferably used.
  • the concentration of the zirconia or titania fine particles in the alcohol dispersion of the zirconia or titania fine particles is not particularly limited, but usually, so that the surface treatment with the silane coupling agent can be performed efficiently, It is in the range of 1 to 40% by weight, preferably in the range of 5 to 30% by weight.
  • the average particle size of the zirconia or titania fine particles in the zirconia or titania fine particle alcohol dispersion is preferably in the range of 1 to 50 nm so that the obtained organic solvent dispersion is excellent in transparency. is there.
  • a silane coupling agent at a temperature in the range of ⁇ 20 to 60 ° C.
  • an acid in an alcohol dispersion of zirconia or titania fine particles as described above.
  • an acid is added to an alcohol dispersion of fine particles of zirconia or titania and stirred at a temperature in the range of ⁇ 20 to 60 ° C. for an appropriate time, for example, 0.5 to 5 hours.
  • a coupling agent is added, and the mixture is stirred at a temperature in the range of ⁇ 20 to 60 ° C. for an appropriate time, for example, 3 to 24 hours, and the zirconia or titania fine particles are thus surface-treated.
  • the temperature at which the acid is added to the alcohol dispersion of fine particles of zirconia or titania and stirred, and the temperature at which the resulting dispersion is surface-treated with a silane coupling agent do not have to be the same.
  • the temperature must be in the range of ⁇ 20 to 60 ° C.
  • the above raw material is present in the presence of an acid.
  • the inorganic oxide fine particles of the dispersion are treated with a silane coupling agent.
  • the acid is preferably an organic acid, and specific examples include, for example, acetic acid, formic acid, butyric acid, caproic acid, caprylic acid, caproic acid, linoleic acid, oleic acid and other aliphatic carboxylic acids, lactic acid, citric acid, tartaric acid, Mention may be made of aliphatic oxycarboxylic acids such as malic acid and ricinoleic acid, and aromatic oxycarboxylic acids such as salicylic acid.
  • Such an organic acid is usually used in an amount of 10 to 200 parts by weight with respect to 100 parts by weight of zirconia or titania in an alcohol dispersion of fine particles of zirconia or titania, and preferably alcohol of fine particles of zirconia or titania. It is used in an amount of 10% by weight or more with respect to zirconia or titania in the dispersion, and 150 parts by weight or less with respect to 100 parts by weight of zirconia or titania in the alcohol dispersion of fine particles of zirconia or titania.
  • an inorganic acid can also be used as the acid that is present when the raw material dispersion is treated with the silane coupling agent.
  • the inorganic acid include sulfuric acid, nitric acid, phosphoric acid and the like. Such an inorganic acid is usually used at a ratio of 0.01 to 1% by weight with respect to zirconia or titania in an alcohol dispersion of fine particles of zirconia or titania.
  • the silane coupling agent used in the present invention has the general formula (I) R n -Si-X 4-n (In the formula, R represents a non-reactive group or a group containing a reactive functional group, X represents a hydrolyzable group or a hydroxy group, and n is 1, 2 or 3.) It is an organosilicon compound represented by.
  • non-reactive group examples include an alkyl group, a cycloalkyl group, a halogenated alkyl group, a phenyl group, and an alkylphenyl group.
  • group containing a reactive functional group examples include an amino group and an epoxy group. And groups containing a group, a vinyl group, a mercapto group, a halogen atom, a (meth) acryloyl group, and the like.
  • non-reactive silane coupling agents having non-reactive groups include, for example, methyltrimethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, diphenyldimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane.
  • reactive silane coupling agents having a group containing a reactive functional group include, for example, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, vinyltrimethoxysilane, and vinyltriethoxysilane.
  • a reactive silane coupling agent having a group containing a reactive functional group and a non-reactive having a halogenated alkyl group, particularly a fluorinated alkyl group.
  • a silane coupling agent is preferably used.
  • vinyltrialkoxysilane such as vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris ( ⁇ -methoxyethoxy) silane, ⁇ - (meth) acryloyloxymethyltrimethoxysilane, ⁇ - (meta ) Acryloyloxymethyltriethoxysilane, ⁇ - (meth) acryloyloxyethyltrimethoxysilane, ⁇ - (meth) acryloyloxyethyltriethoxysilane, ⁇ - (meth) acryloyloxypropyltrimethoxysilane, ⁇ - (meth) acryloyl (Meth) acryloyloxyalkyltrialkoxysilanes such as oxypropyltriethoxysilane, 3,3,3-trifluoropropyltrimethoxysilane, methyl-3,3,3-trifluoropropyld
  • an alcohol dispersion of fine particles of zirconia or titania is treated with a silane coupling agent in the presence of an acid at a temperature in the range of ⁇ 20 to 25 ° C.
  • a silane coupling agent having a fluoroalkyl group
  • such a silane coupling agent is used in the range of 5 to 200 parts by weight with respect to 100 parts by weight of zirconia or titania in the alcohol dispersion of fine particles of zirconia or titania, preferably zirconia or titania. 5 wt% or more, particularly 10 wt% or more with respect to zirconia or titania in the fine particle alcohol dispersion, and 150 weight parts with respect to 100 weight parts of zirconia or titania in the fine particle alcohol dispersion of zirconia or titania. Used in the following ranges.
  • the silane coupling agent when used in an amount exceeding 200 parts by weight based on 100 parts by weight of zirconia or titania, the refractive index of zirconia or titania in the obtained organic solvent dispersion is remarkably lowered.
  • the silane coupling agent when the inorganic oxide fine particles are zirconia, as the silane coupling agent, at least one selected from vinyltrialkoxysilane and (meth) acryloyloxyalkyltrialkoxysilane is preferably used.
  • the silane coupling agent at least one selected from (meth) acryloyloxyalkyltrialkoxysilane and a silane coupling agent having a fluoroalkyl group is preferably used.
  • the obtained dispersion medium of the alcohol dispersion of the inorganic oxide fine particles is used.
  • the alcohol is replaced with a lipophilic organic solvent, and thus a desired organic solvent dispersion of the inorganic oxide fine particles is obtained.
  • Examples of the lipophilic organic solvent include ketones, esters, ethers, hydrocarbons, halogenated carbons, carboxylic acid amides, and the like.
  • Specific examples of ketones include methyl ethyl ketone (MEK), diethyl ketone, methyl isobutyl ketone (MIBK), methyl amyl ketone, and cyclohexanone.
  • Examples of esters include ethyl acetate, butyl acetate, propylene glycol methyl ether acetate, and diethylene glycol.
  • Monoethyl ether acetate, methyl acrylate, methyl methacrylate, etc., ethers include dibutyl ether, dioxane, etc., hydrocarbons include n-hexane, cyclohexane, toluene, xylene, solvent naphtha, etc.
  • halogenated carbon hydrogens include carbon tetrachloride, dichloroethane, chlorobenzene, etc.
  • examples of carboxylic acid amides include dimethylformamide, dimethylacetamide, N-methylpyrrolidone, and the like.
  • the method itself can be performed by a distillation substitution method or an ultrafiltration concentration substitution method which are already well known.
  • the distillation substitution method is a method in which an alcohol dispersion of inorganic oxide fine particles is heated to a temperature equal to or higher than the boiling point of the alcohol to distill and remove the alcohol while adding a desired organic solvent to the dispersion.
  • an alcohol dispersion of inorganic oxide fine particles surface-treated with a silane coupling agent is heated under normal pressure or reduced pressure, the alcohol is distilled, and an organic solvent is added to the dispersion at the same rate as its distillation rate. Can replace the alcohol with the organic solvent.
  • the organic solvent to be used has a boiling point that is the same as or higher than that of the alcohol under the distillation conditions. It is desirable to have.
  • the ultrafiltration concentration and substitution method is a method in which an alcohol dispersion of inorganic oxide fine particles is subjected to ultrafiltration, and the target organic solvent is added to the dispersion while removing the alcohol through a membrane. For example, an alcohol dispersion of inorganic oxide fine particles surface-treated with a silane coupling agent is pumped to an ultrafiltration module, and the alcohol is removed by passing through the membrane, stepwise or continuously.
  • the alcohol can be replaced with the organic solvent by adding an organic solvent to the dispersion.
  • an alcohol dispersion of inorganic oxide fine particles having an average particle diameter of 1 to 50 nm is obtained, depending on the average particle diameter of the inorganic oxide fine particles in the raw material dispersion.
  • the inorganic oxide fine particles are hardly aggregated or the aggregation of the inorganic oxide fine particles is reduced, and the average particle size is usually 1 to 120 nm, preferably 5 to 100 nm.
  • An organic solvent dispersion having a fine particle concentration of 1 to 40% by weight, preferably 5 to 30% by weight can be obtained.
  • an organic solvent dispersion of inorganic oxide fine particles having an average particle diameter of about 3 to 30 nm can also be obtained.
  • the organic solvent dispersion of the obtained inorganic oxide fine particles can further remove the organic solvent by distillation or the like, if necessary, to increase the concentration of the inorganic oxide fine particles.
  • Example 1 Zirconia methanol dispersion (SZR-M manufactured by Sakai Chemical Industry Co., Ltd., zirconia concentration 10% by weight, zirconia average particle diameter 3 nm, total light transmittance 88.1%) and acetic acid (Wako Pure Chemical Industries, Ltd.) 13 g of a reagent special grade) was added and stirred at 50 ° C. for 1 hour. To this dispersion, 4 g of vinyltrimethoxysilane (KBM-1003 manufactured by Shin-Etsu Chemical Co., Ltd.) was added and stirred at 50 ° C. overnight.
  • KBM-1003 manufactured by Shin-Etsu Chemical Co., Ltd.
  • the dispersion treated in this manner is heated under normal pressure to distill methanol, and methyl ethyl ketone (special grade of reagent manufactured by Wako Pure Chemical Industries, Ltd.) is added dropwise to the dispersion at the same rate as the methanol distillation rate. Then, the solvent was replaced, and a methyl ethyl ketone dispersion of zirconia was obtained.
  • Example 2 13 g of acetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) 13 g was added to 100 g of zirconia methanol dispersion (SZR-M manufactured by Sakai Chemical Industry Co., Ltd.) and stirred at 23 ° C. for 1 hour.
  • Example 3 13 g of acetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) 13 g was added to 100 g of zirconia methanol dispersion (SZR-M manufactured by Sakai Chemical Industry Co., Ltd.) and stirred at 50 ° C. for 1 hour. To this dispersion, 2 g of 3-acryloyloxypropyltrimethoxysilane (KBM-5103 manufactured by Shin-Etsu Chemical Co., Ltd.) was added and stirred overnight at 50 ° C.
  • SZR-M zirconia methanol dispersion
  • KBM-5103 3-acryloyloxypropyltrimethoxysilane
  • the dispersion treated in this manner is heated under normal pressure to distill methanol, and methyl ethyl ketone (special grade of reagent manufactured by Wako Pure Chemical Industries, Ltd.) is added dropwise to the dispersion at the same rate as the methanol distillation rate. Then, the solvent was replaced, and a methyl ethyl ketone dispersion of zirconia was obtained.
  • Example 4 13 g of acetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) 13 g was added to 100 g of zirconia methanol dispersion (SZR-M manufactured by Sakai Chemical Industry Co., Ltd.) and stirred at 23 ° C. for 1 hour.
  • Example 5 After adding 200 g of 1-butyl alcohol (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) to 100 g of zirconia methanol dispersion (Sakai Chemical Industry Co., Ltd., SZR-M), concentration using an evaporator is performed to obtain a zirconia concentration. 100 g of a 10% by weight 1-butyl alcohol dispersion was obtained. To 100 g of this dispersion, 13 g of acetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) was added and stirred at 50 ° C. for 1 hour.
  • 1-butyl alcohol special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.
  • the sol treated in this manner is heated under normal pressure to distill 1-butyl alcohol, while the dispersion has the same distillation rate as the above 1-butyl alcohol (special grade manufactured by Wako Pure Chemical Industries, Ltd.). Solvent substitution was performed while dropping toluene at a speed to obtain a toluene dispersion of zirconia.
  • Example 7 Methanol was distilled from a zirconia methanol dispersion (SZR-M manufactured by Sakai Chemical Industry Co., Ltd.) to adjust the zirconia concentration to 30% by weight. To 100 g of this dispersion, 39 g of acetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) was added and stirred at 10 ° C. for 1 hour.
  • Example 8 To 100 g of a zirconia methanol dispersion (SZR-M manufactured by Sakai Chemical Industry Co., Ltd.), 13 g of acetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) was added and stirred at ⁇ 10 ° C. for 1 hour. To this dispersion, 2 g of 3-methacryloyloxypropyltrimethoxysilane (KBM-503 manufactured by Shin-Etsu Chemical Co., Ltd.) was added and stirred overnight at -10 ° C.
  • KBM-503 manufactured by Shin-Etsu Chemical Co., Ltd.
  • the dispersion treated in this manner is heated under normal pressure to distill methanol, and methyl ethyl ketone (special grade of reagent manufactured by Wako Pure Chemical Industries, Ltd.) is added dropwise to the dispersion at the same rate as the methanol distillation rate. Then, the solvent was replaced, and a methyl ethyl ketone dispersion of zirconia was obtained.
  • Example 9 To 100 g of a zirconia methanol dispersion (SZR-M manufactured by Sakai Chemical Industry Co., Ltd.), 50 mg of nitric acid having a concentration of 25% by weight was added and stirred at 50 ° C. for 1 hour.
  • Example 10 Anatase titania methanol dispersion (SAD-M manufactured by Sakai Chemical Industry Co., Ltd., titania concentration 5% by weight, titania average particle diameter 19 nm, total light transmittance 74.3%) and acetic acid (Wako Pure Chemical Industries ( 6.5 g of Reagent special grade, manufactured by KK) was added and stirred at 50 ° C. for 1 hour. To this dispersion, 1 g of 3-methacryloyloxypropyltrimethoxysilane (KBM-503 manufactured by Shin-Etsu Chemical Co., Ltd.) was added and stirred overnight at 50 ° C.
  • Example 11 To 100 g of methanol dispersion of anatase titania (SAD-M manufactured by Sakai Chemical Industry Co., Ltd.), 6.5 g of acetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) was added and stirred at 23 ° C. for 1 hour.
  • Example 12 6.5 g of acetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) was added to 100 g of methanol dispersion of anatase type titania (SAD-M manufactured by Sakai Chemical Industry Co., Ltd.) and stirred at 10 ° C. for 1 hour. To this dispersion, 1 g of 3-methacryloyloxypropyltrimethoxysilane (KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd.) was added and stirred at 10 ° C. overnight.
  • SAD-M anatase type titania
  • KBM-503 3-methacryloyloxypropyltrimethoxysilane
  • the dispersion treated in this manner is heated under normal pressure to distill methanol, and methyl ethyl ketone (special grade of reagent manufactured by Wako Pure Chemical Industries, Ltd.) is added dropwise to the dispersion at the same rate as the methanol distillation rate. While replacing the solvent, a titania methyl ethyl ketone dispersion was obtained.
  • methyl ethyl ketone special grade of reagent manufactured by Wako Pure Chemical Industries, Ltd.
  • the dispersion treated in this manner is heated under normal pressure to distill methanol, and methyl ethyl ketone (special grade of reagent manufactured by Wako Pure Chemical Industries, Ltd.) is added dropwise to the dispersion at the same rate as the methanol distillation rate. While replacing the solvent, a titania methyl ethyl ketone dispersion was obtained.
  • Example 14 6.5 g of acetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) was added to 100 g of a rutile-type titania methanol dispersion (Sakai Chemical Industry Co., Ltd. SRD-M), and the mixture was stirred at ⁇ 10 ° C. for 1 hour.
  • Comparative Example 1 13 g of acetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) 13 g was added to 100 g of zirconia methanol dispersion (SZR-M manufactured by Sakai Chemical Industry Co., Ltd.) and stirred at 23 ° C. for 1 hour. 4 g of vinyltrimethoxysilane (KBM-1003 manufactured by Shin-Etsu Chemical Co., Ltd.) was added to this dispersion, and the mixture was stirred at 65 ° C. overnight.
  • SZR-M zirconia methanol dispersion
  • KBM-1003 vinyltrimethoxysilane
  • the dispersion treated in this manner is heated under normal pressure to distill methanol, and methyl ethyl ketone (special grade of reagent manufactured by Wako Pure Chemical Industries, Ltd.) is added dropwise to the dispersion at the same rate as the methanol distillation rate. Then, the solvent was replaced, and a methyl ethyl ketone dispersion of zirconia was obtained.
  • Comparative Example 2 After adding 200 g of 1-butyl alcohol (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) to 100 g of zirconia methanol dispersion (Sakai Chemical Industry Co., Ltd., SZR-M), concentration using an evaporator is performed to obtain a zirconia concentration.
  • Comparative Example 4 6.5 g of acetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) was added to 100 g of methanol dispersion of anatase-type titania (SAD-M manufactured by Sakai Chemical Industry Co., Ltd.) and stirred at 65 ° C. under reflux for 1 hour. .
  • acetic acid special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.
  • Comparative Example 5 6.5 g of acetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) was added to 100 g of a rutile-type titania methanol dispersion (Sakai Chemical Industry Co., Ltd. SRD-M), and stirred at 65 ° C. under reflux for 1 hour. To this dispersion was added 1 g of trifluoropropyltrimethoxysilane (KBM-7103 manufactured by Shin-Etsu Chemical Co., Ltd.), and the mixture was stirred at 65 ° C. overnight.
  • acetic acid special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.
  • SRD-M rutile-type titania methanol dispersion
  • KBM-7103 trifluoropropyltrimethoxysilane
  • the dispersion treated in this manner is heated under normal pressure to distill methanol, and methyl ethyl ketone (special grade of reagent manufactured by Wako Pure Chemical Industries, Ltd.) is added dropwise to the dispersion at the same rate as the methanol distillation rate. While replacing the solvent, the solvent was replaced. However, the titania methyl ethyl ketone dispersion after solvent substitution was cloudy and precipitation occurred, and a uniform and transparent dispersion could not be obtained.
  • the average particle diameters of the organic dispersions of zirconia and titania used as starting materials in the above Examples and Comparative Examples were measured as follows.
  • the total light transmittance and the average particle diameter of the organic solvent dispersion of zirconia and the organic solvent dispersion of titania obtained in the above examples and comparative examples were measured. The results are shown in Tables 1 and 2.
  • the total light transmittance and average particle diameter of the organic solvent dispersion were measured as follows. Total light transmittance The total light transmittance was measured by filling a cell having an optical path length of 10 mm with a dispersion and using a visible ultraviolet spectrophotometer (V-750 manufactured by JASCO Corporation). Average particle diameter The average particle diameter of the inorganic oxide particles in the dispersion was measured by a dynamic light scattering method using UPA-UT manufactured by Nikkiso Co., Ltd.
  • a zirconia methanol dispersion was treated with a silane coupling agent at a temperature of 65 ° C. in the presence of an acid, and then the dispersion medium was replaced with methyl ethyl ketone to obtain a zirconia organic solvent dispersion.
  • the total light transmittance is 62%.
  • the zirconia methanol dispersion was treated with a silane coupling agent in the presence of an acid at a temperature within the range specified in the present invention, and then the dispersion medium was used.
  • An organic solvent dispersion of titania is obtained, and a uniform and transparent methyl ethyl ketone dispersion can be obtained.
  • the titania methanol dispersion was treated with trifluoropropyltrimethoxysilane at a temperature of 25 ° C. or lower in the presence of an acid, and then the dispersion medium was replaced with methyl ethyl ketone.
  • An organic solvent dispersion having a high light transmittance can be obtained.
  • Example 14 the rutile titania methanol dispersion as the raw material dispersion had a total light transmittance of 46.0%, and the raw material dispersion was treated with trifluoropropyltrimethoxysilane at 10 ° C. After that, by replacing the dispersion medium with methyl ethyl ketone, an organic solvent dispersion having a total light transmittance of 83% can be obtained. In Example 15, an organic solvent dispersion having a total light transmittance of 87% can be obtained by treating the raw material dispersion with trifluoropropyltrimethoxysilane at ⁇ 10 ° C. and then replacing the dispersion medium with methyl ethyl ketone. it can.

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Abstract

La présente invention concerne un procédé de production d'une dispersion de solvant organique extrêmement transparente composée de microparticules d'oxyde inorganique, consistant à mélanger une dispersion alcoolique composée de microparticules d'un oxyde inorganique, choisi parmi la zircone et le titane, avec un agent de couplage au silane en présence d'un acide dans une plage de températures allant de ‑20 à 60°C, traiter en surface les microparticules d'oxyde inorganique par mélange, puis remplacer l'alcool par un solvant organique lipophile.
PCT/JP2010/069392 2009-10-29 2010-10-26 Procédé de production d'une dispersion de solvant organique composée de microparticules d'oxyde inorganique WO2011052762A1 (fr)

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CA2778761A CA2778761A1 (fr) 2009-10-29 2010-10-26 Procede de production d'une dispersion de solvant organique composee de microparticules d'oxyde inorganique
RU2012122027/05A RU2012122027A (ru) 2009-10-29 2010-10-26 Способ получения дисперсии микрочастиц неорганического оксида в органическом растворителе
AU2010312371A AU2010312371A1 (en) 2009-10-29 2010-10-26 Method for producing organic solvent dispersion of inorganic oxide microparticles
EP10826892A EP2495291A1 (fr) 2009-10-29 2010-10-26 Procédé de production d'une dispersion de solvant organique composée de microparticules d'oxyde inorganique
US13/504,330 US20120217456A1 (en) 2009-10-29 2010-10-26 Method for producing dispersion of microparticles of inorganic oxide in organic solvent
CN2010800495184A CN102575124A (zh) 2009-10-29 2010-10-26 无机氧化物微粒的有机溶剂分散体的制造方法
JP2011538514A JP5776552B2 (ja) 2009-10-29 2010-10-26 無機酸化物微粒子の有機溶媒分散体の製造方法

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JP2015081275A (ja) * 2013-10-22 2015-04-27 第一工業製薬株式会社 光半導体用シリコーン樹脂組成物およびその硬化物
JP2015117157A (ja) * 2013-12-18 2015-06-25 レジノカラー工業株式会社 酸化ジルコニウム粒子の非アルコール有機溶媒分散液とその製造方法
WO2016136765A1 (fr) * 2015-02-27 2016-09-01 堺化学工業株式会社 Procédé de production d'une dispersion dans un solvant organique de particules d'oxyde de titane
WO2016136763A1 (fr) * 2015-02-27 2016-09-01 堺化学工業株式会社 Dispersion de particules d'oxyde de titane dans un solvant organique et son procédé de production
JP2016175804A (ja) * 2015-03-20 2016-10-06 住友大阪セメント株式会社 無機酸化物粒子分散液、樹脂組成物、マスターバッチ、樹脂複合体、及び光半導体発光装置
KR20170048404A (ko) 2014-09-05 2017-05-08 사까이가가꾸고오교가부시끼가이샤 산화지르코늄 입자의 유기 용매 분산체와 그 제조 방법
CN110577241A (zh) * 2018-06-07 2019-12-17 北京化工大学 一种形貌可控的透明单分散纳米氧化锆液相分散体的制备方法
WO2021182378A1 (fr) * 2020-03-10 2021-09-16 石原産業株式会社 Particules inorganiques revêtues en surface, procédé pour la production de celles-ci et dispersion de celles-ci dans un solvant organique

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DE102016209499A1 (de) * 2016-05-31 2017-11-30 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Nanostrukturierte Mikropartikel aus silanisierten Primärpartikeln mit steuerbarer Redispergierbarkeit und Verfahren zu deren Herstellung

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JP2013203929A (ja) * 2012-03-29 2013-10-07 Ishihara Sangyo Kaisha Ltd 無機物粒子分散体及びその製造方法
JP2015081275A (ja) * 2013-10-22 2015-04-27 第一工業製薬株式会社 光半導体用シリコーン樹脂組成物およびその硬化物
JP2015117157A (ja) * 2013-12-18 2015-06-25 レジノカラー工業株式会社 酸化ジルコニウム粒子の非アルコール有機溶媒分散液とその製造方法
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KR20170048404A (ko) 2014-09-05 2017-05-08 사까이가가꾸고오교가부시끼가이샤 산화지르코늄 입자의 유기 용매 분산체와 그 제조 방법
KR20170124560A (ko) 2015-02-27 2017-11-10 사까이가가꾸고오교가부시끼가이샤 산화티탄 입자의 유기 용매 분산체와 그 제조 방법
JP6011749B1 (ja) * 2015-02-27 2016-10-19 堺化学工業株式会社 酸化チタン粒子の有機溶媒分散体とその製造方法
JP6028958B1 (ja) * 2015-02-27 2016-11-24 堺化学工業株式会社 酸化チタン粒子の有機溶媒分散体の製造方法
KR20170124561A (ko) 2015-02-27 2017-11-10 사까이가가꾸고오교가부시끼가이샤 산화티탄 입자의 유기 용매 분산체의 제조 방법
WO2016136763A1 (fr) * 2015-02-27 2016-09-01 堺化学工業株式会社 Dispersion de particules d'oxyde de titane dans un solvant organique et son procédé de production
US9963355B2 (en) 2015-02-27 2018-05-08 Sakai Chemical Industry Co., Ltd. Method for producing organic solvent dispersion of titanium oxide particles
WO2016136765A1 (fr) * 2015-02-27 2016-09-01 堺化学工業株式会社 Procédé de production d'une dispersion dans un solvant organique de particules d'oxyde de titane
US10047239B2 (en) 2015-02-27 2018-08-14 Sakai Chemical Industry Co., Ltd. Organic solvent dispersion of titanium oxide particles and method for producing same
JP2016175804A (ja) * 2015-03-20 2016-10-06 住友大阪セメント株式会社 無機酸化物粒子分散液、樹脂組成物、マスターバッチ、樹脂複合体、及び光半導体発光装置
CN110577241A (zh) * 2018-06-07 2019-12-17 北京化工大学 一种形貌可控的透明单分散纳米氧化锆液相分散体的制备方法
CN110577241B (zh) * 2018-06-07 2020-11-03 北京化工大学 一种形貌可控的透明单分散纳米氧化锆液相分散体的制备方法
WO2021182378A1 (fr) * 2020-03-10 2021-09-16 石原産業株式会社 Particules inorganiques revêtues en surface, procédé pour la production de celles-ci et dispersion de celles-ci dans un solvant organique

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